| Dirty Angels | Kevn Kinney | 3:14 | |
| No More Crying The Blues | The Cactus Blossoms | 2:03 | |
| The Sudbury Nickel | John Doe, The Sadies | 1:20 | |
| Desperate & Depressed | Margo Price | 3:31 | |
| To Get By | Malcolm Holcombe | 4:03 | |
| Give Back the Key to My Heart | Uncle Tupelo | 3:26 | |
| Meltdown | Slobberbone | 3:35 | |
| Jesus Was a Social Drinker | Chuck Prophet | 4:54 | |
| Freight Train | Dexateens | 2:05 | |
| Soldiering On | Mary Gauthier | 5:32 | |
| It Just Dawned on Me | John Doe, The Sadies | 2:33 | |
| Self Destructive Zones | Drive-By Truckers | 4:12 | |
| South Georgia Sugar Babe | Justin Townes Earle | 2:47 | |
| Boxcar | Shovels & Rope | 4:41 | |
| Wingless Angels | Bow Thayer, Levon Helm | 4:06 | |
| Meet Me on the Corner | Motel Mirrors, Amy LaVere, John Paul Keith | 2:30 | |
| Jane Doe | Sarah Shook & the Disarmers | 4:28 | |
| My Old Drunk Friend | Freakwater | 3:33 | |
| El Paso | The Gourds | 3:10 | |
| Monday (Everytime I Turn Around) | The Bottle Rockets | 3:45 | |
| Yum Yum | The Deslondes, Riley Downing, Dan Cutler, Sam Doores, Cameron Snyder | 2:56 | |
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| Through Strange Eyes | The Sadies | 2:52 | |
| Outlaw for You | Alejandro Escovedo | 3:26 | |
| Run-down Neighborhood | Lindi Ortega | 3:06 | |
| What It Takes to Break a Heart | The Hello Strangers | 3:26 | |
| Learning to Lose (feat. Willie Nelson) | Margo Price, Willie Nelson | 6:19 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| Black Bitter Moon | Malcolm Holcombe, Iris DeMent | 2:59 | |
| JP's Florida Blues #1 | JP Harris | 3:06 | |
| Gasoline and Matches | Buddy & Julie Miller, Buddy Miller, Julie Miller | 3:14 | |
| Pass You By - Alternate Version | Gillian Welch | 3:55 | |
| Bad Time To Be An Outlaw | The Bottle Rockets | 3:13 | |
| Crippled & Crazy | Scott H. Biram | 3:24 | |
| Tennessee Sun | The Kernal | 4:05 | |
| Too Bad | Lilly Hiatt | 3:11 | |
| Kinky Hypocrite | Drive-By Truckers | 3:13 | |
| Change Your Ways or Die | The Cactus Blossoms | 3:25 | |
| Gawd Above | John Fullbright | 3:37 | |
| Hard On You | Daniel Romano | 3:27 | |
| What You Gonna Do Leroy | Buddy & Julie Miller, Buddy Miller, Julie Miller | 3:45 | |
| Worth Dyin' For | Gurf Morlix | 4:42 | |
| Barrel Chested | Slobberbone | 4:14 | |
| Oval Room | Blaze Foley | 4:04 | |
| Ford Econoline | Chuck Prophet | 3:41 | |
| Johnny Cash | Fred Eaglesmith | 3:20 | |
| Washashore Cowgirl | Monica Rizzio | 3:05 | |
| Evening Gown | Alejandro Escovedo | 3:28 | |
| Boxcars - 2022 Remaster | Joe Ely | 3:59 | |
| Tobacco Road | Colvin & Earle | 2:49 | |
